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Abstract:

Preparation of chiral heterocyclic compounds of the thiadiazoline types, starting from natural terpenones such as fenchone, camphor and menthone, is described. Stereochemical assignment of the compounds synthesized was performed by NMR spectroscopy and X-ray analysis.

Registro:

Documento: Artículo
Título:Behavior of thiosemicarbazones derived from some terpenones under acetylating conditions
Autor:Brousse, B.N.; Moglioni, A.G.; Alho, M.M.; Álvarez-Larena, Á.; Moltrasio, G.Y.; D'Accorso, N.B.
Filiación:Dpto. de Qca. Orgánica, Facultad de Farmacia y Bioquimica, Universidad de Buenos Aires, Argentina
Dpto. de Qca. Orgánica, Fac. de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Argentina
Unitat de Cristal.lografia, Universitat Autonoma de Barcelona, 08193 Bellaterra, Barcelona, Spain
Palabras clave:Asymmetric spiro-heterocyclic compounds; Terpenones; Thiadiazolines; Thiosemicarbazones; 1,3,3 trimethyl 2 norcamphanone; camphor; heterocyclic compound; menthone; n [aza(1,7,7 trimethylbicyclo[2.2.1]hept 2 ylidene)methyl]acetamide; terpene derivative; thiadiazoline derivative; thiosemicarbazone derivative; unclassified drug; acetylation; article; carbohydrate synthesis; carbon nuclear magnetic resonance; chirality; proton nuclear magnetic resonance; stereochemistry; structure analysis; X ray diffraction
Año:2002
Volumen:2002
Número:10
Página de inicio:14
Página de fin:23
Título revista:Arkivoc
Título revista abreviado:Arkivoc
ISSN:14246376
CAS:1,3,3 trimethyl 2 norcamphanone, 1195-79-5; camphor, 464-49-3, 76-22-2, 8008-51-3; menthone, 10458-14-7, 8014-79-7, 89-80-5
PDF:https://bibliotecadigital.exactas.uba.ar/download/paper/paper_14246376_v2002_n10_p14_Brousse.pdf
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_14246376_v2002_n10_p14_Brousse

Referencias:

  • Popov, S.A., Denisov, A.Y., Gatilov, Y.V., Bagryanskaya, I.Y., Tkachev, A.V., (1994) Tetrahedron Asymmetry, 5, p. 479
  • Martins Alho, M.A., Moglioni, A.G., Brousse, B., Moltrasio Iglesias, G.Y., D'Accorso, N.B., (2000) Arkivoc, 1 (4), p. 627. , hptt://www.arkat.org/journal/Issue4/ms0062/ms0062.htm
  • Blumenkopf, T.A., Harrington, J.A., Koble, C.S., Bankston, D.D., Morrison Jr., R.W., Bigham, E.C., Styles, V.L., Spector, T., (1992) Journal of Medicinal Chemistry, 35, p. 2306
  • Sidwell, R.W., Huffman, J.H., Schafer, T.W., Shipman, C., (1990) Chemotherapy, 36, p. 58
  • Teitz, Y., Ronen, D., Vansover, A., Stematsky, T., Riggs, J.L., (1994) Antiviral Research, 24, p. 305
  • Ali, S., Alam, M., (1994) Archives of Pharmaceutical Research, 17, p. 131
  • Martins Alho, M.A., D'Accorso, N.B., (2000) J. Heterocyclic Chem., 37, p. 811
  • Martins Alho, M.A., D'Accorso, N.B., (2000) Carbohydr. Res., 328, p. 481
  • Oppolzer, W., (1987) Tetrahedron, p. 1969
  • Aitken, R.A., Kilényi, S.N., (1992) Asymmetric Synthesis, , Blackie Academic & Professional, Glasgow
  • Somogyi, L., (1991) Liebigs Ann. Chem., p. 1267
  • Gamble, D.L., Hems, W.P., Ridge, B., (2001) J. Chem. Soc., Perkin Trans. I, p. 248
  • Shamsuzzaman, M.A., Anwar, S., (1998) J. Chem. Res., p. 824
  • Sheldrick, G.M., SHELXS-86 (1985) Crystallographic Computing 3, , Sheldrick, G. M.; Krüger, C.; Goddard R., Oxford University Press: Oxford
  • Sheldrick, G.M., (1997) SHELXL-97. Program for the Refinement of Crystal Structures, , Göttingen

Citas:

---------- APA ----------
Brousse, B.N., Moglioni, A.G., Alho, M.M., Álvarez-Larena, Á., Moltrasio, G.Y. & D'Accorso, N.B. (2002) . Behavior of thiosemicarbazones derived from some terpenones under acetylating conditions. Arkivoc, 2002(10), 14-23.
Recuperado de https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_14246376_v2002_n10_p14_Brousse [ ]
---------- CHICAGO ----------
Brousse, B.N., Moglioni, A.G., Alho, M.M., Álvarez-Larena, Á., Moltrasio, G.Y., D'Accorso, N.B. "Behavior of thiosemicarbazones derived from some terpenones under acetylating conditions" . Arkivoc 2002, no. 10 (2002) : 14-23.
Recuperado de https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_14246376_v2002_n10_p14_Brousse [ ]
---------- MLA ----------
Brousse, B.N., Moglioni, A.G., Alho, M.M., Álvarez-Larena, Á., Moltrasio, G.Y., D'Accorso, N.B. "Behavior of thiosemicarbazones derived from some terpenones under acetylating conditions" . Arkivoc, vol. 2002, no. 10, 2002, pp. 14-23.
Recuperado de https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_14246376_v2002_n10_p14_Brousse [ ]
---------- VANCOUVER ----------
Brousse, B.N., Moglioni, A.G., Alho, M.M., Álvarez-Larena, Á., Moltrasio, G.Y., D'Accorso, N.B. Behavior of thiosemicarbazones derived from some terpenones under acetylating conditions. Arkivoc. 2002;2002(10):14-23.
Available from: https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_14246376_v2002_n10_p14_Brousse [ ]